Your hip New York City friend is in town for the weekend, but his suitcase is lost somewhere between here and La Guardia. The simple solution: Book it to this tiny Bucktown men’s boutique, which boasts an exclusive collection of pricey clothing including Seize sur Vingt dress shirts ($188-$210), skater-esque Trovata pants ($150) and Paul Smith jackets ($500-$600). For wannabe trendsetters who need some fashion advice, the always-stylish salespeople can put together a smashing outfit in minutes.
The Churchill Park is bound to be one of the more heavily trafficked entrances to the Bloomingdale Trail. For one, the park has long been a popular spot for area canines and humans looking to play. Secondly, this gateway to the 606 is the closest to the heart of Wicker Park, one of the major culture hubs on the North Side. The neighborhood is loaded with rock venues, taco restaurants, nightclubs, boutiques and galleries. Oh, in case you're wondering, the park is not named for Winston Churchill, but rather the Churchill Cabinet Company, which owned the lot up until 1973.
RECOMMENDED: Our complete guide to the 606